Q 3P - Organic Chemistry (Mcmurry)

Question

How many products might be formed on chlorination of o-xylene (o-dimethylbenzene), m-xylene, and p-xylene?

Step-by-Step Solution

Answer

Chlorination of o-xylene

Chlorination of meta-xylene

Chlorination of para-xylene

Step1: Xylene

Xylene or dimethyl benzene is an aromatic compound that contains two methyl groups attached as substituents to the ring. It has three types of isomers as follows:

Step 2: Chlorination of o, m, and p-xylene

In o-xylene, the two methyl groups are ortho/ para directing in nature. The methyl group shows a +I (inductive) effect and it activates the incoming group at the o/p position in the ring. Chlorination of o-xylene results in two products as shown:

Chlorination of meta-xylene results in three products as shown:

In the case of p-xylene, there are two methyl groups in the opposite position to each other, so the incoming chlorine group could join at only one position and a single ortho product is formed which is as shown: